This is a difficult concept for some who have grown up products of the modern, everyone-gets-a-trophy era. Failure? “I refuse to fail,” one mentee once told me. I admired her fortitude (she’s a very accomplished tennis player), and then asked her if she’d ever lost a match. “Well……yes,” she said, but went on to describe a burning desire to never fail again. Jack Nicklaus (still the greatest golfer of all time) genuinely believes he never missed a putt he had to make. These are mindsets that are common in high achievers.

The obsession with not failing, though, can be debilitating.

Circa 2006, I took over a team that had been led by a “zero tolerance” manager, and on the first day, I could literally see and feel the paralysis in the room. One young team member approached me at the lunch break. “Give me one thing I can do right away that will make me better,” he said. “Make a mistake every day,” I told him. “Then stop what you’re doing, call me, tell me what the mistake was, and let’s figure out how we can get better because of it.”

He looked at me for about ten seconds. “Can I speak freely?” he asked his new boss. “Always,” I replied. “That’s crazy talk!” he blurted.

But it ain’t crazy talk.

“Playing tight,” or taking the safe route can slow us down and curb our growth. When we’re resisting our instincts or fighting the current, it might well be time to just take a flyer, try a new approach or do something we’ve never done before to see if we can get closer to the outcome we’re seeking. And we might fail. When we do, hopefully, we have someone we can call, who’ll celebrate the failure with us and help us figure out how we can get better because of it.

We certainly don’t want people repeating the same mistakes. But if we ain’t failing, we ain’t trying hard enough. We might not get a trophy. Some peers might snicker, and some might bluster about our ineptitude. They’ll be wrong, and probably jealous. As Beckett says, “No matter. Try again. Fail again. Fail better.” When we take that approach, we’ll continually get better, and make a bigger difference, day-after-day.